Herbicides 1-aliphatic-3-aryl-5-imino imidazolidine-2,4-diones and imidazolidine-2-one-4-thiones

ABSTRACT

5-IMINO-IMIDAZOLIDINEDIONES AND 4-THIO-5-IMINOIMIDAZOLIDINEDIONES IN WHICH THE NITROGEN IN THE 1 POSITION OF THE IMIDAZOLIDINEDIONE NUCLEUS IS SUBSTITUTED WITH AN ARYL RADICAL OF SIX TO 15 CARBON ATOMS, THE NITROGEN IN THE 3 POSITION IS SUBSTITUTED WITH AN ALIPHATIC OR CYCLOALIPHATIC RADICAL AND THE IMINO GROUP IS OTPIONALLY SUBSTITUTED WITH A CARBAMOYL OR Nchloroacetylcarbamoyl radical. These imidazolidinediones are preand post-emergence herbicides.

United States Patent Singer Oct. 23, 1973 [54] HERBICIDES 3,287,467 11/1966 Gerjowich 260/3067 l ALIPHATIC 3 ARYL S IMINO 3,632,599 1/1972 Zsch0cke.... 71/92 X 3,696,115 10/1972 Zschocko 71/92 X lMIDAZOLlDlNE-2,4-DIONES AND 1M1DAZOLIDINE-2-ONE-4-THIONES Inventor: Malcolm S. Singer, Richmond, Calif.

Assignees Chevron Research Company, San

Francisco, Calif.

Filed: Nov. 4, 1971 Appl. No.: 195,872

Related U.S. Application Data Division of Ser. No. 852,509, Aug. 22, 1969, Pat. No. 3,655,689, which is a continuation-in-part of Ser. No. 745,417, July 17, 1968, abandoned.

[52] US. Cl. 71/92 [51] Int. Cl A01n 9/22 [58] Field of Search 71/92 [56] References Cited UNITED STATES PATENTS 3,287,466 11/1966 Klopping 260/306] Primary Examiner-James 0. Thomas, Jr. Att0rneyJ. A. Buchanan, John Stoner, Jr. and Raymond Owegang 57 ABSTRACT 5-imino-imidazolidinediones and 4-thio-5-iminoimidazolidinediones in which the nitrogen in the l position of the imidazolidinedione nucleus is substituted with an aryl radical of six to 15 carbon atoms, the ni-\ trogen in the 3 position is substituted with an aliphatic or cycloaliphatic radical and the imino group is 0tpionally substituted with a carbamoyl or N- chloroacetylcarbamoyl radical. These imidazolidinediones are preand post-emergence herbicides.

12 Claims, No Drawings v HERBICIDES 1-ALIPHATIC-3-ARYL-5-IMINO IMIDAZOLIDINE-2,4-DIONES AND IMIDAZOLIDINE-2-ONE-4-THIONES CROSS REFERENCE TO RELATED APPLICATION application Ser. No. 745,417, filed July 17, 1968, now

abandoned.

FILED OF INVENTION This invention relates to novel imidazolidinediones and their use as herbicides.

DESCRIPTION OF INVENTION The novel imidazolidinediones of this invention may be represented by the formula Y= =N-IR wherein Y is a chalocogen atom of atomic number eight to 16, i.e., O or S, R contains one to about carbon atoms, and is aliphatic or cycloaliphatic with the proviso that when Y is S, R is alkyl or cycloalkyl of the above-mentioned carbon content, R contains six to about carbon atoms, and is aryl nuclearly substituted with O to 1 trifluoromethyl and/or 0 to 2 halogens of atomic number nine to 35, i.e., F, Cl and Br, nitro groups, alkyl of one to four carbon atoms, each or alkoxy groups individually having one to four carbon atoms and R is hydrogen, acetyl or carbamoyl in which the nitrogen is singly substituted with alkyl of one to 10 carbon atoms, chloroacetyl or R R may be substituted with O to 1 halogen of atomic number 17 to 35 or alkoxy of one to four carbon atoms. Of course, when R represents a cycloaliphatic radical it contains a minimum of 3 carbon atoms. Preferably R contains one to six carbon atoms and is an unsubstituted alkyl or unsubstituted cycloalkyl radical, R is phenyl substituted with O to 1 trifluoromethyl and/or 0 to 2 halogens of atomic number nine to 35, nitro groups, alkyl of one to four carbon atoms, or alkoxy of one to four carbon atoms and R is hydrogen.

, Examples of radicals which R may represent are alkyl such as methyl, ethyl, isopropyl, butyl, hexyl, nonyl and decyl; cycloalkyl such as cyclopropyl, cyclobutyl, cyclohexyl and cyclooctyl; alkenyl such as allyl, pentenyl and'hexenyl; cycloalkenyl such as cyclohexenyl; alkynyl such as propargyl; chloromethyl, bromomethyl, methoxyethyl, ethoxyethyl, chlorocyclohexyl, bromocyclohexyl and p-methoxycyclohexyl.

Typical radicals which R may represent are phenyl, tolyl, xylyl, cumyl, naphthyl, benzyl, phenylethyl, phenylbutyl, o-butylphenyl, 3,5-dipropylphenyl, o-, mand p-chlorophenyl, 0-, mand p-fluorophenyl, o-, mand p-bromophenyl, 3,5-dibromophenyl, 2,6-

difluorophenyl, 2-fluoro-4-bromophenyl, 3-chloro-5-' fluorophenyl, 3-ch1oro-5-propoxyphenyl, 2-fluoro-4,5- dimethyl-phenyl, 3-chloro-5-butylphenyl, pchlorobenzyl, 2,6-dimethyl-4-trifluoromethylphenyl, 3-methyl-5-propoxyphenyl, S-trifluoromethylnaphthyl, 5,8-dimethylnaphthyl, 2,4- dichlorophenyl, o-, mand p-methoxyphenyl, o-, mand p-nitrophenyl, p-butoxyphenyl 2,4-dinitrophenyl, 2-fluoro-5-nitrophenyl, p-othoxyphenyl, 6- chloronaphthyl, 6-bromonaphthyl, 6-nitronaphthyl, 3,7-dichloronaphthyl, 2-methoxynaphthyl, 4- ethylnaphthyl, 2-nitro-4-trifluoromethylphenyl, 0-, mand p-trifluoromethylphenyl, 3-chloro-5-trifluoromethylphenyl, 2,6-difluoro-4-trifluoromethylphenyl, 2- bromo-S-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3-trifluoromethylphenyl-5- methoxyphenyl, 3-butoxy-5-trifluoromethylphenyl and 2,5-difluoro-4-trifluoromethylphenyl.

In the imidazolidinediones of this invention in which R is carbamoyl in which the nitrogen is substituted with alkyl, the alkyl may be branched or straightchained. Such alkyl groups include methyl, ethyl, propyl, isobutyl, hexyl, S-methylheptyl, n-octyl and ndecyl. Alkyl of one to six carbon atoms is preferred.

.Illustrative imidazolidinediones of this invention are 1-phenyl-3-methyl-4-thio-5-imino-2,4- imidazolidinedione, 1-p-bromophenyl-3-isopropyl-5- imino-2 ,4-imidazo1idinedione 1-( 2 4-dichlorophenyl)-3-chloromethyl-5-imino-2,4- imidazolidinedione, l-xylyl-3-methoxypropyl-4-thio-5- imin0-2,4-imidazolidinedione, l-o-bromophenyl-3- cyclohexyl-5-imino-2,4-imidazolidinedione, l-pnitrophenyl-3-cyclobutyl-5-imino-2,4-

imidazolidinedione, 1-o-fluorophenyl-3 4 bromocyclohexyl)-4-thio-5-imino-2,4-

imidazoladinedione, 1-naphthyl-3-hexyl-5-imino-2 ,4- imidazolidinedione, l-(6-chloronaphthyl)-3-allyl-5- imino-2,4-imidazolidinedione, 1-(6-nitronaphthyl)-3- hexeny1-5-imino-2,4-imidazolidinedione, l-( 3 5-dinitrophenyl)-3-butoxyethyl-4-thio-5-imin0-2,4- imidazolidinedione, l-p-methoxyphenyl-3-cyclobutyl- 4-thio-5-imino-2,4-imidazolidinedione, 1-oethoxyphenyl-3-bromoethyl-5-imino-2,4- imidazolidinedione, l-m-butoxyphenyl-3 -methyl-4- thio-5-imino-2,4-imidazolidinedione, 1-( 3 4'-dibromopheny1)-3-decyl-4-thio-5-imino-2,4-. imidazolidinedione, l-p-fluorophenyl-3-propargyl-5- imino-2,4-imidazolidinedione, 1 1-( 6'methoxynaphthyl)-3-methyl-5-imino-2,4- imidazolidinedione, 1-phenyl-3-(4-chlorocyclohexyl)- 4-thio-5-imino-2,4-imidazolidinedione, l-phenyl-3- methyl-4-thio-5-N-methylcarbamoy1imino-2,4- imidazolidinedione, l-(2', 4'-dichlorophenyl)-3 hexyl- 5-N-buty1carbamoylimino-2,4-imidazolidinedione, l -pnitrophenyl-3-allyl-S-N-octylcarbamoylimino-2,4- imidazolidinedione, l-p-methoxyphenyl-3-cyclohexyl- 5-N-ethylcarbamoyliminc-2,4-imidazolidinedione, 1- (6-chloronaphthyl)-3-methyl-4-thio-5-N- decylcarbamoylimino-2,4-imidazolidinedione, phenyl-3-cyclohexenyl-5-N-phenylcarbamoylimino- 2,4-imidazolidinedione, 1-p-fluorobenzyl-3-isopropyl- 5-imino-2,4-imidazolidinedione, l-( 3 -methoxy-5 trifluoromethylphenyl)-3-butyl-5-imino-2,4- imidazolidinedione, 1-(6-fluoronaphthyl)-3-ethyl-4- thio-S -imino-2,4-imidazolidinedione, l-( 2 '-fluoro-4 '-npropylphenyl)- 3-allyl-5-imino-2,4-imidazolidinedione, 1-( 3 '-nitro-5 -tri-fluoromethylphenyl )-3-( 2 '-butenyl 5-imino-2,4-imidazolidinedione, 1 l-(2, 6-difluoro-4'-trifluoromethylphenyl)-3-methyl-5- imino-2,4-imidazo1idinedione, chlorophenyl)-3-hexyl-5-imino-2,4- imidazolidinedione, 1-p-fluoro-3-cyclohexyl-5-imino- V imidazolidinedione,

3 2,4-imidazolidinedione, l-p-trifluoromethylphenyl-3- cyclobutyl--imino-2,4-imidazolidinedione, l-( 3 nitro-S '-fluorobenzyl )-3-cyclopropyl-5-imino-2 ,4- imidazolidinedione, l-phenyl -3-octyl-4thio-5-N- hexylcarbamoylimino-2,4-imidazolidinedione, l-pfluorophenyl-3-cyclohexyl-5-N- rnethylcarbamoylimino-2,4-imidazolidinedione, l-(2, 4'-dichlorophenyl)l3-ethyl-4-thio-5-N-acetylimino- 2,4-imidazolidinedione, l-(3', 5-dinitrophenyl)-3- decyl-4-thio-5-N-acetylimino-2,4-imidazolidinedione, 1-(2', 4'-dimethoxyphenyl)-3-methyl-4-thio-5-N- acetylimino-2,4-imidazolidinedione, l-(2'-methoxy-5- nitrophenyl)-3-cyclohexyl-5-N-acetylimino-2,4-

1-p-ethylphenyl-3-methyl-4-thio- 5-N-ethylcarbamoylimino-2,4-imidazolidinedione, lm-butylphenyl-3-ethyl-4-thio-5-N-pchlorophenylcarbamoylimino-Z,4-imidazolidinedione, l'-phenyl-3-methyl-4-thio-5-N-mfluorophenylcarbamoylimino-2,4-imidazolidinedione, l-m-trifluoromethylphenyl-3-heptyl-5-N-pnitrophenylcarbamoylimino-2,4-imidazolidinedione, l-p-tolyl-3-butyl-5-N-( 3 5 -diethoxyphenyl)carbamoylimino-2,4- imidazolidinedione l-m-propylphenyl-3-pchlorocyclohexyl-4-thio-5-N-p-trifluoromethylphenylcarbamoylimino-2,4- imidazolidinedione, l-(2'-methyl-4'-ethylphenyl)-3- methyl-4-thio-S-N-p-tolylcarbamoylimino-2,4- imidazolidinedione and l-p-bromophenyl-3-ethyl-5-N- (3', 5-di-bromophenyl)carbamoylimino-2,4- imidazolidinedione.

The imidazolidinediones of the above formula in which R is hydrogen may be prepared by reacting a lcyanoformamide or l-cyanothioformamide with an isocyanate in the presence of a base catalyst according to the following equation:

C i JCH1Cl.

Excess R CNO, low temperatures and higher catalyst concentrations favor making compounds of the formula In such instances the reaction product may be a mixture of (2) and (3) above. The formation of (3) is particularly favored where R is an unsaturated aliphatic radical.

Preferred base catalysts which may be used are tertiary amines such as triethyl amine and tributyl amine. These catalysts will be used in catalytic amounts, usually about 0.001 to 0.1 mol per mol of reactant. This reaction is exothermic and the temperature will usually be controlled within the range of 0 to 50C. While in most instances the reactants are miscible, it is desirable to carry out the reaction in polar, aprotic solvents such as dimethoxyethane, tetrahydrofuran, acetonitrile, dimethylformamide and dimethyl sulfoxide.

These compounds and their preparation are further illustrated by the following examples. These examples are intended to illustrate the invention described herein and are in no manner intended to limit it. Unless otherwise indicated, percentages are by weight.

EXAMPLES Example 1 4.9 g. of N-ethyl-l-cyanoformamide were mixed with 6.7 g. p-tolylisocyanate and 5 ml. dimethoxyethane in a vessel at ambient temperature. Two drops of triethylamine were added to this solution. The temperature of the reaction mixutre rose but the temperature was kept below about 50C. After exothermicity subsided about 20 ml. of ethanol were added and the mixture was scratched and cooled, causing some crystallization. 10 ml. benzene and about 50 ml. petroleum ether were then added to form a precipitate. The reaction mixture was then filtered and the solids dried, leaving 6 g. of l-ptolyl-3-ethyl-5-imino-2,4-imidazolidinedione. This compound was observed as a crystalline solid melting at l07-1llC. Its nitrogen analysis was: Theoretical 18.20 percent; Found 18.00 percent.

Example 2 N-methyl-l-cyanothioformamide was prepared by mixing a benzene solution of methylisothiocyanate with aqueous potassium cyanide, allowing the mixture to stand at ambient temperature, extracting the aqueous layer with chloroform in the presence of H* and removing the chloroform from the extract.

6.5 g. of l-(3,4-dichlorophenyl)-3-methyl-4-thio-5- imino-2,4-imidazoliclinedione was made by reacting 3.0 g. of N-methyl-l-cyanothioformamide with 5.0 g. of 3,4-dichlorophenyl-isocyanate by the general procedure of Example 1. This compound was observed as a crystalline solid melting at l -l88C. Its Cl and S analyses were:

Theoretical Found S: 11.11% ll.25% Example 3 6.3 g. of N-allyl-l-cyanothioformamide, 6.0 g. of phenylisocyanate and 3.5 g. of dimethoxyethane were mixed in a vessel of ambient temperature. Two drops of triethylamine were added to the solution causing an extremely exothermic reaction. After 10 minutes the dimethoxyethane was removed leaving a red solid. This red solid was washed with ethanol and filtered. The solids were then recrystallized from a dimethoxyethaneethanol mixture to give 2-3 g. of l-phenyl-3-allyl-4- thio-S-N-phenylcarbamoylimino-2,4- imidazolidinedione. This compound was observed as a crystalline solid melting at 215-217C. lts N and S Example 5 analyses were: 11 g. of 1-phenyl-3-methyl-4-thio-5-iminc-2,4-

imidazolidinedione and 50 ml. dimethoxyethane were Theoretical pound charged to a vessel. Ketene was added to the mixture N: 15-38% 15-30% 5 for minutes at a rate of 0.1 mol/hr. Two drops of S: 897% H 80 were then added and ketene was bubbled through the mixture at the above rate for another hour. Example 4 A solid precipitate formed which was filtered from the mixture. 7.1 g. of solid product was thus obtained. In- 10.15 g. of l-phenyl-3-methyl-5-imino-2,4-imidaz0li- 10 frared analysis of this solid and melting point comparidinedione and g. of dimethoxyethane were charged sons indicated it was l-phenyl-3-methyl-4-thio-5- to a vessel. 6.0 g. of chloroacetylisocyanate was added acetylimino-2,4-imidazolidine-dione. It melted at to this mixture. The 1-phenyl-3-methyl-5-imino-2,4- 197200C. Its N and S analyses were: imidazolidinedione dissolved as the mixture became warm. Two drops of triethylamine were added after 20 5 Theoreical Fmmd N: l6.05% 15.62% S:

minutes. Crystallization occurred slowly after cooling. 1215a, 12,0091,

The precipitate was filtered and washed with dimethoxyethane. 12.5 g. of l-phenyl-3-methyl-5- l-phenyl-3-methyl-5-acetylimino-2,4-

chloroacetylcarbamoylimino-2,4-imidazolidinedione imidazolidinedione was similarly prepared by treating was thus collected. This material melted at 20 l-phenyl-3-methyl-5-imino-2,4-imidazolidinedione 198-202C. Its N and Cl analyses were: with ketene.

By the general procedure described in Examples 1, 3 and 4 other imidazolidinediones of this invention were ff 5's,: :31 prepared. These compounds and their analyses are re- Cl: 11.00% 10.60% 25 ported 1n Table 1.

TABLE I Element analyses Melting N 01 point, Compound C. Cale. Found Cale. Found 1-p-ch1or0phenyl-3-n-buty1-5-imin0-2,4-irnidazolidinedione -72 15 .03 14 .12 12.70 12 .45 1-phenyl-3-cycl0hexyl-5-imin0-2,4-imidaz01idinedi0ne 78-79 15.5 .10 1-p-n1tropheny1-3-methyl-5-imino-2,4-imidaz01idinedi0ne 183-185 22 .56 1-p-meth0xypheny1-3methy1-5imino-2,4-imidazolidinedione 158-159 18 .0 l-p-nitrophenyl-3-ethyl-5-imino-2,4-imidazolidinedione -143 21 .38 1-(3,4-dich10rophenyl)-3-methyl-5-imino-2,4-imidazolidinedione. -154 15 .45 l-m-t01y1-3methy1-5-imin0-2,4-imidaz0lidinediOne 130-137 19 .38 1-p-to1y1-3-methy1-5imino-2,4-irnidazolidinedione 164-167 19 .38 1-phenyl-B-cyclohexy1-5-imin0-2,4-imidazolidinedione 78-79 15 .5 1-m-chlor0pheny1-3-methy1-5-imine-2,4-imidaz01idinedione 134-137 17 .70 1-phenyl-3-methyl-5-imino-2,4-imidaz01idinedione 150-153 20.7 1-(3,4-dich10rophenyl)-3-ethy1-5-imin0-2,4-imidazolidinedione 94-97 14 .69 1-p-ch1orophenyl-3-allyl-5-imin0-2,-imidazolidinedione 97-100 15 .95 1-p-chlor0pheny1-3-11-buty1-5-imin0-2,4-imidazolidinedione 70-72 15 .03 1 -0-fiuoroph eny1-3-methy1-4-thi0-5-o-flu0r0pheny1carbam0y12,4-imid 198-200 14 .95 1-p-methyoxypheny1-3-ethy1-5-imino-2,4-imidaz0lidienedione 95-98 17 .01 1-p-chl0r0phenyl-3-ethyl-5-imino-2,4-imidazolidinedione 111-115 16.70 1 -m-ch1oropheny1-3-methyl-4-th10-5-imino-2A-imidazolidinedione. 147-149 **12 .62 1 -m-ehl0rophenyl-3-ethy1-5-imin0-2,4-imidazolidinedione 62-66 16 .70

l-m-bromophenyl-3-methyl-4-thio-5-im1no-2,4-imidazolidinedione- 1-(2,4-difluor0phenyll-3-metl1yl-5-imin0-2,4-irnidazolidi nedione. l-phenyl-B-meth yl-4-thi0-5-phenylcarbarnoylimino-Z ,4-imidazolidined1one...

1-0-fluorophenyl-irmethy1-4-thi0-5-chl0roacety1carbamoylimino-2,4-imidaz0l1dinedione 1-phenyl-3-methyl-4-thio-5-ch10r0acetylcarbarnoylimin0-2,4-imidaz0lidinedione 1-(2-flu0ro-5-trifluoromethylphenyl)-3-methyl-4-thio-5-imino-2,4-imidazo1idinedione 1-(4-chl0r0-3trifluorornethylphenyl)-3-methy1-4-thio5-1min0-2,4-imidazolidinerlione 121-125 9.95 1-(4-fiu0r0-3'-trifluoromethy1phenyD-3-methyl-4-thi0-5-imin0-2,4-imidazolidinedione 147-151 "11.48

Fluorine. Sulfur. *Bmmine.

' imidazolidinediones will be applied in herbicidal quantities to the environment, e.g., soil infested with seeds and/or seedlings of such vegetation. Such application will inhibit the growth of or kill the seeds, germinating seeds and seedlings. They are applied directly to the foliage and other plant parts in post-emergence applications. They are effective against weed grasses as well as broadleaved weeds.

The uniqueness of the imidazolidinediones of this invention is evidenced by the fact that known corresponding compounds wherein the substituents R and R in the above formulas are of the same subgenus, e.g., both aryl or both aliphatic, exhibit little, if any, herbicidal activity.

Pre-emergence herbicidal tests on representative imidazolidinediones of this invention were made using the following method.

An acetone solution of the test imidazolidinedione was prepared by mixing 750 mg. imidazolidinedione, 220 mg. surfactant and 5 ml. acetone. This solution was added to c.a. 125 ml. water containing 156 mg. surfactant.

Seeds of the test vegetation were planted in a pot of soil and the imidazolidinedione solution was sprayed uniformly onto the soil surface at a dose of 100 micrograms per cm". The pot was watered and placed in a greenhouse. The pot was watered intermittently and observed for seedling emergence, health of emerging seedlings, etc., for a 3-week period. At the end of this period the herbicidal effectiveness of the imidazolidinedione was rated based on the physiological observations. A O to 100 scale was used; representing no phytotoxicity, 100 representing complete kill. These test results appear in Table II.

For comparison several known compounds in which R and R in the above formulas are radicals of the same subgenus were also tested. The test results on these comparison compounds also appear in Table II.

" TABLE II Herbicidal eflectlveness Compound W M l L 1-p-t0lyl-3-ethyl-5-imin0-2,4-imiz1azolldinedlonu 100 100 100 1-(3,4-dlchlorophenyl)-3-methyl-4-thi0'5-imln0- 2,4-imidazolidinedlone 100 100 100 100 1-phenyl-3-cyc1ohexyl-5-imine-2,4

dinedione 99 99 99 99 l-p-methoxyphenyl-3-methy1-5-imino-2,4-

imidazolidinedione 100 100 100 100 1-m-chl0r0phenyl-3-methyl-5-imin0-2,4-

imidazolidinedione 100 100 100 100 1-phenyl-3-methyl-5-imin0-2,4-irnidazo1idinedione 100 100 100 100 1-(3,4-dichlorophenyl)-3-methyl-5-imin0-2A- imidazolidinedione 100 100 100 L00 1-m-tolyl-3-methy1-5-imin0-2,4-imjdazolidinedione 100 100 100 100 l-m-chloropheny1-3-methyl-5-imin0-2,4-

imidazolidinedione 100 100 100 100 1-(3,4-dichl0rophenyI-3-ethyL5-imino-2,4

imidazolidinedione 100 100 100 l-p-chlorophenyl-3-allyl-5-imin0-2,4-imidazolidinedione 100 100 100 l-(rn-trifluoromethyl henyD-3-methyl-4-thio-5- imino-2,4-imidazol.i 'nedione 100 100 100 100 1-(4 fiuoro-3-triflu0r0methylphenyl)-3-methyl- I 5-imino-2,4-imidazolidinedione 100 100 100 100 1-(4-chloro'3-trifluoromethylphenyl)-3-methyl- 5-imino-2,4-lmidazolidinedione 100 100 100 100 1-(2-fiuoro-5-trifiuoromethylphenyl)-3-methyl- 5-imine-2,4-imidazolidinedi0ne 100 100 100 100 l-(o-trifluoromethyl henyl)-3-methyl-4-thio-5- imin02,4-irmdazo idinedioneuu u 80 60 50 60 TABLE II-Contlnued Horbicidnl elfectlvoncss Compound W M 1 L 1-(5-fluoro-2-methylphonyl)-3-methyl-4-thio-5- imin0-2,4-imidazolidinedione 100 100 100 100 l-(3-fiuoro-4-methylphenyl)-3-mcthyl-4-thi0-5- imin0-2,4'imidazolidlncdionc 100 100 100 100 1-phenyli methyl-4-thio-5-imino-2,4-imidazolidinedione 100 100 100 100 l-p-chloro henyl-3-methyl'4-thi0-5-imino-2A- imidazoidinedlono H 100 100 100 100 l-p-fluorophenyl-3-methyl-4-thi0-5-imin0-2,4-

imidazolidinedione 100 100 100 100 l-o-chloro henyl-B-methyl-4-thi0-5-imino-2,4-

imidazoidinedione 96 99 99 90 1-o-flu0rophenyl-3-methyl-4thio-5-imine-2,4-

imidazolidinedione 100 100 100 100 l-o-fluorophenyl-Ii-methyl-5-imin0-2,4-

imidazolidinedione 100 100 100 100 1-m-nitr0phenyl-3-methy1-5-imino-2,4-

imidazolidinedione 100 100 l-m-bromopheny1-3-methyl-5-imino-2,4-

imidazolidinedione 100 100 100 100 1-(5-fluoro-2-rnethylphenyl)-3-methyl-5- imino-ZA-imidazolidinedione 99 100 100 100 1-(3-fluoro-4-methylphenyl)-3-rnethyl-5- imin0-2,4-imidazo1idinedione 100 100 100 100 1-(4-fiuoro-3-methylphenyl)-3-methyl-5- imino-2,4-imidazolidinedione 100 100 100 100 l-m-bromophenyl-3-methyl4-thio-5-imino-2,4-

imidazolidinedione 100 100 100 100 1-(2-,4-difiu0rophenyl)-3-methyl-5-imin0-2,4-

imidazolidinedione 100 100 100 100 1-phenyl-3-methyl-4thlo-5-phenylcarbamoylimin0-2,4-lmldazolidinedlone 100 U!) 99 l-phenyl-S-methyl-fi-ch oroacetylcarbamoyl- 1min0-2,4-imldazolidlnedlnno 100 100 100 100 lofluorophcnyl-3-methyl4-thlo-fi-uhloroacotylcarbamoyliminc-2,4-imidazolidinediono. 100 100 100 100 l-phonyl-B-methyl-4-thio-fi-chloroacntylcarbamoylimin0-2,4-imldazolldinedione 100 100 100 100 1-(2-flu0ro-b-trifluor0methylphenyl)-3-methyl- 4-thi0-5-imin0-2,4-imidazolldlnodione 100 100 100 100 1-(4-chl0r0-3'-tr flu0romethy1phenyl)-3- methyl-4-thi0-5-imino-2A-imidazolidinediono 70 100 100 100 1-(4-fiu0ro-3-trifiuoromethylphenyl)-3- methyl-4-thi0-5-imin0-2,4-imidazolidinedi0ne 90 100 100 100 l-p-chloro henyl-3-ethyl-5-imino-2,4-

imidaz0idinedione 100 100 100 100 l-m-chlorophenylJi-meth imidazolidinedione. 100 100 100 100 1-m-chlorophenyl-3-ethyl-5-imino-2,4-

imidazolidinedione 100 100 100 1-p-fluorophenyl-3-methyl-5-imino-2,4-

imidazo'dinedione 100 100 100 100 1-m-chlorophenyl-3-allyl-5-imine-2,4-

imidazolidinedione 100 100 100 l-phenyl-3-n-butyl-5-imino-2,4-

imidazolidinedione 100 0 100 1-phenyl-3-allyl-5-imino-2,4imidazolidinediono.. 100 100 100 100 COMPARISON 1,3-dimethyl-5-imino-2A-imidazolidinedione 0 0 0 0 l-m-chlorophenyl-(i-phenyl-4thi0-5'imin0-2,4-

imidazolidinedione 4 0 0 0 1,3-di(4-nitr0phenyl)-5-imin0-2,4-

imidazolidinedione 0 22 10 10 1-pmeth0Xyphenyl-3-phenyl-4-thi0-5-imin02,4-

imidazolidinedione 0 0 0 0 W=Watergrass (Echinochloa cruagalli). M=Mustartl (Brasaica arvensia). P=Pigweed (Amarrmllms rclmjlezua). L=Lambsquarter (Chrrnopodium album).

The data of Table II illustrate the specificity of the substituents on the nuclear nitrogens of the imidazolidinediones of this invention. It is truly unexpected and surprising that these substituents must be from differ ent genera in order for the compounds to exhibit any significant herbicidal effectiveness.

The amount of imidazolidinedione administered will vary with the particular plant part or plant growth medium which is to be contacted, the general location of application, i.e., sheltered areas such as greenhouses as compared to exposed areas such as fields, as well as the desired type of control. For preemergent control of most plants dosages in the range of about 0.5 to 20 lbs. per acre will be used. Such administration will give a concentration of about 2 to 80 ppm. imidazolidinedione distributed throughout 0.1 acre-foot. For post-emergence application, such as foliar spray application, compositions containing about O.5 to 8 lbs imidazolidinedione per 100 gal. spray will be used. Such application is equivalent to about 0.5 to 20 lbs. imidazolidinedione per acre.

The herbicidal compositions of this invention comprise a herbicidal amount of one or more of the above described imidazolidinediones intimately admixed with a biologically inert carrier. The carrier may be a liquid diluent such as water or acetone or a solid. The solid may be in the form of dust, powder or granules. These compositions will also usually contain adjuvants such as a wetting or dispersing agent to facilitate their penetration into the plant growth media or plant tissue and generally enhance their effectiveness. These compositions may also contain other pesticides, stabilizers, conditioners, fillers and the like.

I claim:

1. An herbicide composition comprising an herbicidal quantity of a compound of the formula Y= =N-R3 wherein Y is a chalcogen atom of atomic number eight to 16, R is alkyl of one to 10 carbon atoms, cycloalkyl of three to eight carbon atoms, alkenyl of three to six carbon atoms, cyclohexenyl or propargyl, the same being substituted with to 1 halogen of atomic number nine to 35 or alkoxy of one to four carbon atoms, with the proviso that when Y'is S, R is alkyl or cycloalkyl, R contains a total of six to 15 carbon atoms, and is phenyl substituted with 0 to l trifluoromethyl and/or 0 to 2 halogens of atomic number nine to 35, nitro groups, alkyl groups of one to four carbon atoms or alkoxy groups individually having one to four carbon atoms and R is hydrogen, acetyl or carbamoyl in which the nitrogen is singly substituted with alkyl of one to carbon atoms, R or chloroacetyl; admixed with a biologically inert carrier therefor.

2. The composition of claim 1 wherein R is an unsubstituted alkyl of l to 6 carbon atoms or unsubstituted cycloalkyl radical of three to six carbon atoms, R is phenyl substituted with 0 to 1 trifluoromethyl and/or 0 to 2 halogens of atomic number nine to 35, nitro, alkoxy of one to four carbon atoms or alkyl of one to four carbonatoms and'R is hydrogen.

3. The composition of claim 1 wherein Y is oxygen, R is methyl, ethyl, butyl, allyl, or cyclohexyl, R is phenyl, tolyl, chlorophenyl, fluorophenyl, nitrophenyl, methoxyphenyl or dichlorophenyl and R is hydrogen.

4. The composition of claim 1 wherein R is carbamoyl in which the nitrogen is singly substituted with alkyl of one to six carbon atoms.

5. The composition of claim 1 wherein the compound is l-o-fluorophenyl-3-methyl-4-thio-5-imino-2,4- imidazolidinedione.

6. The composition of claim 1 wherein the compound is l-o-fluorophenyl-3-methyl-5-imino-2,4- imidazolidinedione.

7. A method for controlling undesirable vegetation which comprises applying to said vegetation or the environment of said vegetation an herbicidally effective amount of a compound of the formula Y: =N--R wherein Y is a chalcogen atom of atomic number eight to 16, R is alkyl of one to 10 carbon atoms, cycloalkyl of three to eight carbon atoms, alkenyl of three to six carbon atoms, cyclohexenyl or propargyl, the same being substituted with O to l halogen of atomic number nine to 35 or alkoxy of one to four carbon atoms, with the proviso that when Y is S, R is alkyl or cycloalkyl, R contains a total of six to 15 carbon atoms and is phenyl substituted with 0 to l trifluoromethyl and/or 0 to 2 halogens of atomic number nine to 35, nitro groups, alkyl groups of one to four carbon atoms or alkoxy groups individually having one to four carbon atoms and R is hydrogen, acetyl or carbamoyl in which the nitrogen is singly substituted with alkyl of one to 10 carbon atoms, R or chloroacetyl; admixed with a biologically inert carrier.

8. The method of claim 7 wherein R is an unsubstituted alkyl of one to six carbon atoms or unsubstituted cycloalkyl radical of three to six carbon atoms, R is phenyl substituted with 0 to 1 trifluoromethyl and/or 0 to 2 halogens of atomic number nine to 35, nitro, alkoxy of one to four carbon atoms or alkyl of one to four carbon atoms and R is hydrogen.

9. The method of claim 7 wherein Y is oxygen, R is methyl, ethyl, butyl, allyl, or cyclohexyl, R is phenyl, tolyl, chlorophenyl, fluorophenyl, nitrophenyl, me-

thoxyphenyl or dichlorophenyl and R is hydrogen.

The method of claim 7 wh erein R is carbamoyl in which the nitrogen is singly substituted with alkyl of I 

2. The composition of claim 1 wherein R1 is an unsubstituted alkyl of 1 to 6 carbon atoms or unsubstituted cycloalkyl radical of three to six carbon atoms, R2 is phenyl substituted with 0 to 1 trifluoromethyl and/or 0 to 2 halogens of atomic number nine to 35, nitro, alkoxy of one to four carbon atoms or alkyl of one to four carbon atoms and R3 is hydrogen.
 3. The composition of claim 1 wherein Y is oxygen, R1 is methyl, ethyl, butyl, allyl, or cyclohexyl, R2 is phenyl, tolyl, chlorophenyl, fluorophenyl, nitrophenyl, methoxyphenyl or dichlorophenyl and R3 is hydrogen.
 4. The composition of claim 1 wherein R3 is carbamoyl in which the nitrogen is singly substituted with alkyl of one to six carbon atoms.
 5. The composition of claim 1 wherein the compound is 1-o-fluorophenyl-3-methyl-4-thio-5-imino-2,4-imidazolidinedione.
 6. The composition of claim 1 wherein the compound is 1-o-fluorophenyl-3-methyl-5-imino-2,4-imidazolidinedione.
 7. A method for controlling undesirable vegetation which comprises applying to said vegetation or the environment of said vegetation an herbicidally effective amount of a compound of the formula
 8. The method of claim 7 wherein R1 is an unsubstituted alkyl of one to six carbon atoms or unsubstituted cycloalkyl radical of three to six carbon atoms, R2 is phenyl substituted with 0 to 1 trifluoromethyl and/or 0 to 2 halogens of atomic number nine to 35, nitro, alkoxy of one to four carbon atoms or alkyl of one to four carbon atoms and R3 is hydrogen.
 9. The method of claim 7 wherein Y is oxygen, R1 is methyl, ethyl, butyl, allyl, or cyclohexyl, R2 is phenyl, tolyl, chlorophenyl, fluorophenyl, nitrophenyl, methoxyphenyl or dichlorophenyl and R3 is hydrogen.
 10. The method of claim 7 wherein R3 is carbamoyl in which the nitrogen is singly substituted with alkyl of one to six carbon atoms.
 11. The method of claim 7 wherein the compound is 1-o-fluorophenyl-3-methyl-4-thio-5-imino-2,4-imidazolidinedione.
 12. The method of claim 7 wherein the compound is 1-o-fluorophenyl-3-methyl-5-imino-2,4-imidazolidinedione. 